Process of producing 1-dimethylamino-2-methylbutene-3.



is heated on a boiling GEORG MEELING. OF ELBEB-FELD, AND

COLOGNE, GERMANY, ASSIGNORS TO FARBENFABRIKEN VORM.

CORPORATION OF GERMANY.

& (30., OF ELBERFELD. GERMANY, A

HUGO KOHLER, OF LEVEBKUSEN, NEAR FRIEDR. BAY ER PROCESS OF PRODUCING 1-DIMETHYLAMINO-2-METHYLBUTEll'E-3.

No Drawing.

To all whom it may concern:

Be it known that we, Gnono MERLING and Hum KoHLEn, doctors of philosophy, chem ists, citizens of the German Empire, residing, respectively, at Elberfeld and Lever kusen, near Cologne, (:ermany, have invented new and useful Improvements in' Processes of Producing l-Dimethylamino-Q- Methylbutene-ii, of which the following is a specification.

The present invention concerns the production of 1-dimethylamino-Q-methylbutene-3 (beta-methylisocrotyldirnethylamiul having most probably the formula:

which has proved to be a valuable intermediate product for the manufacture of isoprene. The process for its production consists in heating 2-methyl-3-oxybutyldimethylamin.

CH3-CH-.CH(CH;-CH;N(CH;)1

with a dehydrating agent and more specifically with sulfuric acid as dehydrating agent.

in order to illustrate the new process more fully the following example is given, the parts being by weight 1 part of .Z-methyl- 3-oxybutyldimcthylami is heated in an autoclave with 5-40 parts of sulfuric acid per cent.) for 10 hours to 150-160 C. After coolin the solution is saturated with caustic soda yo and the unsaturated base is distilled with steam, isolated and after being dried with caustic potash purified by distillation.

The elimination of water from the oxybase proceeds more quickly and more easily on treating the oxybase with concentated sulfuric acid.

1 part of 2.-methyl-3-oxybutyldimethyl amin is gradually dropped into 3 parts 0 concentrated sulfuric acid which has to be cooled and stirred and the colorless solution water bath for 3 to 4 hours. The brownish solution is poured on ice, saturated while being cooled with caustic soda lye and worked up in the same manner as before described. The yield of l-dimethylarnino-Q-methylbutene-3 is nearly Specification of Letters Patent.

Patented June 17, 1913.

Application filed November 7, 1912. Serial No. 730,018.

theoretical. tone-3 is a colorless thin soluble in Water having a resembling coniin and l-dimethylamino-Q-niethylbuliquid, diiiicultly penetrating odor boiling at from e claim 1 v 1. Process for producing l-diniethylamino-2-mcthylbutene-3 which comprises dehydrating 2 methyl 3 oxybutyldimethylamin. i

2. Process for producing l-dimethylamino-2-methylbutene-3 which comprises heating 2-methyl-3-oxybutyldimethylamiu with a dehydrating agent.

3. Process for producing l-dimethylamino-2-methylbutene-3 which comprises heating 2-methyl-3-oxybutyldimethylamm with concentrated sulfuric acid.

4. Process for producing l-dimethylamino-Q-methylbutene-S having most probably the formula:

onZ which process consists in first heating 2- 1nethyl-3-ox butyldimethylamin ens-cu ou ou, -cu, s cnn on with sulfuric acid and then isolating the resulting base, substantial y as described.

Process for producing l-dlmethylamino-Q-methylbutcnc fi having most prob-' ably the formula:

on, cru=ca-unborn-N on, which process consists in first heating 2- methyl3-oxybutyldimethylaniint orn-ca-cmcunfcm-mcua. (in

with concentrated sulfuric acid and then isolating the resulting base, substantially as described. v

In testimony whereof we have hereunto set our hands 1n the presence of two sub scribing witnesses.

GEORG MERLING. [its] HUGO KOHLER. 1.9. Witnesses HELEN NUFER, ALBERT Norm. 

